Refine Search
Sort by
$925,000
5 Beds 4 Baths
Escape to your own private retreat on 5.41 acres while enjoying the convenience of being just minutes from restaurants, shopping and the beach. Tucked away from the road, this custom-built 5-bedroom, 3.5-bath home features an open floor plan with 10-foot ceilings, hardwood flooring throughout the main living areas, and a living room with a gas fireplace. The chef's kitchen is equipped with a Monogram gas range, pot filler, pantry, abundant cabinetry, and a breakfast area, while the formal dining room and bright three-season room provide additional gathering spaces. The privately situated primary suite offers a peaceful retreat with a spacious ensuite bath and walk-in closet. Two additional bedrooms, a full bath, and a half bath complete the main level, while the upper level provides two more bedrooms and another full bath, ideal for guests or multigenerational living. Outside, enjoy the tranquil setting with a decorative stone pond and mature landscaping. The impressive 40' x 60' metal outbuilding with electric and two 10-foot overhead doors offers incredible flexibility, whether you need a workshop, space for a home business, storage for boats, RVs, classic cars, or recreational equipment. An attached two-car garage, multi-zone HVAC, and fresh interior paint completed in September 2025 complete this exceptional property.

12089 Saint Martins Neck Rd, Bishopville

Listing courtesy of Hileman Real Estate-Berlin. Contact: (410) 208-9200

$899,000
3 Beds 3 Baths
Model-home perfection awaits in this beautifully maintained 3-bedroom, 3-bath home on nearly a half-acre in the sought-after Golf Club Shores III community. Meticulously maintained and beautifully updated, this home showcases true pride of ownership and presents like a model home. Step inside to discover spacious, light-filled living areas thoughtfully designed for both everyday living and entertaining. The immaculate interior features stylish finishes, an inviting floor plan, and exceptional attention to detail throughout. Outside, the expansive lot provides plenty of room to relax, entertain, garden, or simply enjoy the peaceful surroundings. With nearly a half-acre of beautifully maintained property, you'll appreciate the privacy and space this home offers. Golf Club Shores III is a quiet, established neighborhood in Berlin, just minutes from West Ocean City and the area's beaches, dining, shopping, and attractions. Known for its spacious wooded homesites, scenic setting, and proximity to the Ocean City Golf Club, the community offers a tranquil lifestyle with no mandatory HOA. Move-in ready and impeccably cared for, this exceptional home combines comfort, quality, and an outstanding location, making it a rare opportunity you won't want to miss.

11412 Quillin Way, Berlin

Listing courtesy of Newport Bay Realty. Contact: 4102137040

$379,900
3 Beds 2 Baths
Welcome to 15 Lord Guy Terrace, a beautifully maintained one-level home in Ocean Pines. Ideally located just minutes from the beaches of Ocean City and Assateague Island, charming downtown Berlin, championship golf courses, marinas, shopping, dining, and year-round entertainment, this home offers the perfect blend of coastal living and everyday convenience. Situated on an oversized lot with a spacious paved driveway, the property features low-maintenance landscaping with brick-bordered stone beds, a welcoming front porch, and a side porch ideal for outdoor dining and entertaining. Inside, the open-concept layout connects the living room, dining area, and kitchen, creating an inviting space for gathering. The owner's suite is privately positioned at the front of the home, while two guest bedrooms and a full bath are located at the rear. A spacious bonus room off the kitchen provides exceptional flexibility as a second living area, home office, playroom, or potential fourth bedroom with minimal modifications. Ocean Pines offers an impressive selection of resort-style amenities with both free and paid membership options are available. The amenities include swimming pools, parks, playgrounds, walking trails, a championship golf course, marina, yacht club, pickleball and tennis courts, a community garden, and a vibrant community center. This home is an excellent choice for a primary residence, vacation getaway, or investment property. Daily conveniences—including grocery stores, pharmacies, healthcare, banks, and local restaurants—are just minutes away. Enjoy easy access to Ocean City's famous Boardwalk and beaches, Assateague Island National Seashore's wild horses and natural beauty, historic downtown Berlin's boutiques and cafés, numerous nearby golf courses, like Rum Pointe Seaside Golf Links, the Links at Lighthouse Sound, and Glen Riddle Golf Club, boating, fishing, and outdoor recreation, as well as Delaware beach destinations like Lewes, Rehoboth Beach, Bethany Beach, and Fenwick Island all within a 20-50 minute drive.

15 Lord Guy Terrace, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777

$229,000
Create the home you've always envisioned on this 4.57-acre approved building lot, offering plenty of room to spread out and enjoy country living without sacrificing convenience. Whether you're planning a custom residence, a detached workshop, recreational space, or room for gardening and outdoor entertaining, this property provides the flexibility to make it your own. Ideally situated just minutes from Berlin, Ocean City, and Assateague Island, you'll enjoy easy access to award-winning beaches, dining, shopping, golf, and countless outdoor activities. With no HOA restrictions and no city taxes, you'll have the freedom to build and enjoy your property the way you choose. Opportunities like this—offering acreage, privacy, and a prime coastal location—are becoming increasingly difficult to find. Bring your builder and start turning your dream into reality. Perc on file (also in documents tab) No HOA restrictions Currently in crops on a verbal lease agreement Certified by the County as ready to build, just need SRA surveyor- staked on site and submit a Septic Permit Application

Dinges Rd, Berlin

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440

$364,900
3 Beds 3 Baths
A lovely home, a great location, and a great price! Tucked in the serene confines of Sherwood Forest, and yet only a short distance to South Gate of Ocean Pines, this charming 3 Bedroom, 2.5 bath home features 2 FIRST FLOOR bedrooms. One first floor bedroom features an en suite half bath, the full bath is in the hall for both bedrooms to share. Upstairs there is a bedroom, full bath, and a large bonus room with plenty of possibility. Just some of the many features in this home are an open floor plan, updated kitchen with stainless steel appliances, updated bathrooms, gas fireplace, and beautiful LVP floors through the living room, sunroom, and kitchen. Outside there is a deck on the front of the home, a balcony in the rear. Plus a paved driveway and a storage shed. This home is just what you are looking for, schedule a showing today!

7 Royal Oaks Dr, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$914,900
7 Beds 5 Baths
A truly rare opportunity in the heart of Midtown Ocean City! Just one block from the beach, 104 Bering Rd offers an exceptional property featuring two separate homes on one lot—a unique offering that's seldom available in Ocean City. Whether you're looking for a primary residence with guest accommodations, a vacation retreat for extended family, or an investment with incredible flexibility, the possibilities are endless. Lovingly maintained by a caring owner, this property blends classic Old Ocean City coastal charm with thoughtful modern updates. Its prime Midtown location puts you within walking distance of restaurants, shopping, entertainment, 94th Street Park, and just around the corner from the Caribbean Dr. public boat ramp. The MAIN HOME offers approximately 1,508 sq. ft. with 3 bedrooms and 2.5 baths. Step inside to a bright sunroom with tile flooring and abundant natural light. The cozy living room features a gas fireplace, while the beautifully updated kitchen (2021) boasts granite countertops, white cabinetry, and stainless steel appliances. The spacious first-floor primary suite offers hardwood flooring and a beautifully updated bath with a large vanity and tiled shower. A second full bath with a tiled shower, washer & dryer, and hardwood flooring throughout most of the first floor completes the main level. Upstairs you'll find two generously sized bedrooms and a convenient half bath. The GUEST HOME offers approximately 1,000 sq. ft. with 4 bedrooms and 1.5 baths, along with a welcoming front deck. The first floor includes three bedrooms with hardwood flooring, a full bath, half bath, and a washer & dryer. Upstairs features an open living and dining area with hardwood flooring, a fully equipped kitchen with tile flooring, an additional bedroom, and a spacious screened porch overlooking the backyard. The outdoor space is truly something special. Tucked behind the main home is a private, fenced backyard area that feels like your own personal retreat, complete with a large paver patio, covered patio, side yard, multiple storage sheds with lighting, and plenty of room to entertain, eat crabs, BBQ, relax, and create lasting memories with family and friends. Additional highlights include a large driveway providing ample parking. Whether you're searching for a beach getaway, multi-generational living, rental income potential, or simply a one-of-a-kind Ocean City property, 104 Bering Rd is an opportunity you won't want to miss.

104 Bering Rd, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382

$158,490
2 Beds 1 Baths
Updated, Turn-key 2BR/1BA home on a large lot. * * * Location qualifies for 100% Financing!* * * Many updates include replacement vinyl windows, ductless mini-split heat and air conditioning units, architectural-shingled roof, flooring throughout - carpet and LVP, fresh paint. Just a 1/2 mi to Historic Downtown Pocomoke - a charming small town with rich history, art scene, boutique shops - even its own movie theatre - public parks and boat docks, & unique restaurants on the banks of the Pocomoke River. 20mi to NASA Wallops Facility, 20mi to beloved Chincoteague Island, and the incredible wild horses and sandy Atlantic beaches of Assateague. Close to everything Worcester County has to offer - boating, world-class fishing, crabbing, wildlife estuaries, incredible state parks - a true paradise for nature lovers, photographers, boaters - anyone who wants to enjoy the more relaxed pace of the Eastern Shore. Just 2-3 hours to major metro areas - Virginia Beach/Norfolk, Washington DC, Baltimore, Philadelphia, NYC. Life in Worcester County is good - from the beaches to the bays & beyond! NOTE - Number on house is 704; however, the parcel address is 706 5th St. There used to be a house with the house number 706 to the left/south of 704. Owners are licensed realtors. Sizes, taxes, distances approximate.

706 5th St, Pocomoke City

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$1,200,000
4 Beds 3 Baths
Just five minutes outside of Berlin, this 75± acre property offers the kind of space and privacy that’s getting harder to find. The property features a comfortable 2,368 sq ft 4br 2.5 bath home paired with a versatile pole barn, making it ideal for a wide range of uses—whether you’re looking for a working farm, a recreational retreat, or a private homestead with room to grow. The land itself is the real highlight: a sprawling mix of open ground and natural areas that could support farming, hunting, horses, or future expansion. With this much acreage this close to town, you get the rare combination of convenience and seclusion. Whether you’re dreaming of a farmette-style setup, a full-scale homestead, or simply a quiet place to escape the noise, this property delivers flexibility and long-term potential in one of the most desirable rural pockets near Berlin.

Ironshire Station Rd, Berlin

Listing courtesy of The Land Group. Contact: (410) 934-3478

$699,900
5 Beds 3 Baths
Wow! This custom-built 5-bedroom, 3-full-bath home offers the perfect combination of quality craftsmanship, space, and privacy on 3.45 beautifully maintained acres, just minutes from Ocean Pines, Berlin, and Ocean City. Enjoy peaceful golf course views from your backyard overlooking Ocean Resorts Golf Club while experiencing the tranquility of country living with the convenience of nearby beaches, shopping, dining, and entertainment. Designed for both everyday living and entertaining, the open-concept floor plan features a custom kitchen with hardwood floors that flows seamlessly into the spacious living area. Enjoy casual meals in the eat-in kitchen or host family gatherings in the formal dining room, which also makes an ideal home office or flex space. The first-floor primary suite offers a relaxing retreat with a spacious en-suite bath and walk-in closet. Four additional generously sized bedrooms, three full baths, oversized closets, and abundant storage provide room for family, guests, hobbies, or multigenerational living. Step outside to enjoy the expansive deck overlooking the above-ground pool, where you can relax, entertain, or simply take in the scenic golf course views. A blacktop driveway provides plenty of parking and adds to the home's curb appeal. Sold mostly furnished, this move-in-ready home offers exceptional value, combining custom construction, acreage, privacy, and an unbeatable location close to everything the Eastern Shore has to offer.

10671 Cathell Rd, Berlin

Listing courtesy of Sheppard Realty Inc. Contact: (410) 723-7070

$350,000
3 Beds 2 Baths
Price Improvement!!! This beautiful 3-bedroom 2-bath home with plenty of natural light and open concept is the home you have been waiting for! Home features LVP flooring throughout which is highly durable and offers the look of natural wood. Newly painted interior, side deck and new flooring in primary bedroom and second bedroom as well as a brand-new water heater completes all the updates needed for a turnkey home. Enjoy your peaceful and relaxing screened in-porch as it is the perfect indoor/outdoor oasis that expands your living space. Living area includes a fireplace for those cool fall or winter evenings, and the kitchen boasts plenty of cabinet space and a pantry. This home also includes an attached storage area for tools, beach chairs, bicycles or whatever you may want to store!

1218 Ocean Pkwy, Ocean Pines

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382

$949,000
4 Beds 3 Baths
Featuring over $80,000 in brand-new capital upgrades—including a brand-new bulkhead, new dock, new roof, and newer dual zone HVAC system with full ductwork—this premier Wood Duck Isle estate offers immediate boating access with absolute structural peace of mind. Perfectly positioned near the end of a canal with beautiful views stretching across Manklin Creek, this spacious 4-bedroom, 2.5-bath waterfront home offers the ideal blend of comfort, quality, and coastal living. Meticulously maintained and thoughtfully updated, the current owners have invested extensively in the home's major systems and waterfront features. Designed for both everyday living and entertainment, the first floor features a spectacular waterfront primary suite with a beautifully updated bathroom and an oversized walk-in closet. A dramatic two-sided brick gas fireplace creates a warm focal point, shared between the primary bedroom and the dining room. The main level also includes a spacious waterfront great room with hardwood flooring, a sunroom filled with natural light, a private den or study, a powder room, and a well-appointed kitchen conveniently located just beyond the mudroom/laundry room, which connects directly to the oversized two-car garage. Brand new SS Kitchen appliances to be installed at the end of August. Upstairs are three distinctive bedrooms and an updated full bathroom, providing plenty of space for family and guests, along with easily accessible attic storage. Step outside to embrace the waterfront lifestyle with an 8,000-pound boat lift, professionally enhanced with numerous mechanical upgrades. Whether you're heading out for a day on the water or simply relaxing while taking in the peaceful creek views across Manklin Creek, this property is a true boater's retreat. If you've been searching for a meticulously maintained waterfront home with lovely views, generous living spaces, exceptional updates, and easy boating access, this is an opportunity you won't want to miss!

74 Wood Duck Dr, Ocean Pines

Listing courtesy of ERA Martin Associates, Shamrock Division. Contact: 4106415000

$260,000
3 Beds 3 Baths
Brand NEW 3BR/2.5BA - poplar Meadowbrooke 2-story floorplan with spacious great room, kitchen w/granite counters, and roomy dining area. A half bath w/granite counters and laundry room complete the first floor. Upstairs, Primary bedroom with walk-in closet, and full, en-suite bath - granite counters on the double-sink vanity, step-in shower. 2 additional bedrooms, and a 2nd full bath w/tub/shower combo and granite-topped vanity. Upgrades galore included in list price -- granite kitchen and bathroom counters, stainless steel kitchen appliance package -- built-in microwave, electric stove/range, fridge, dishwasher, and stylish upgraded white kitchen cabinets, LVP flooring through the living, dining, kitchen, and baths, ceiling fans in every bedroom and the living room. Neutral, welcoming color palette to enhance with your decor, or a nice, light base to make it your own. Half mile to Historic Downtown Pocomoke - a charming small town with rich history, art scene, charming shops - even its own movie theatre - public parks and boat docks, & unique restaurants on the banks of the Pocomoke River. Location qualifies for 100% Financing! 19mi to NASA Wallops Facility, 18mi to beloved Chincoteague Island, and the incredible wild horses and sandy Atlantic beaches of Assateague. Close to everything Worcester County has to offer - boating, world-class fishing, crabbing, wildlife estuaries, incredible state parks - a true paradise for nature lovers, photographers, boaters - anyone who wants to enjoy the more relaxed pace of the Eastern Shore. Just 2-3 hours to major metro areas - Virginia Beach/Norfolk, Washington DC, Baltimore, Philadelphia, NYC. Life in Worcester County is good - from the beaches to the bays & beyond! Sizes, taxes approximate - taxes do not reflect the home being completed. *** Please note - ANY & ALL Plans, renderings, sizes, descriptions, listings, acreages are all for REFERENCE only, and may show upgrades & options not included in list price. Owner is a licensed realtor.

621 Cedar St, Pocomoke City

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$249,995
3 Beds 1 Baths
Completely Renovated Eastern Shore Gem! Welcome to this beautifully renovated 3-bedroom, 1-bath home, where nearly every detail has been updated within the last two years, giving you the peace of mind and style of a much newer home without the new construction price tag. From the gorgeous kitchen and updated bathroom to the flooring, finishes, fixtures, and mechanical improvements, this home is truly move-in ready. Perfectly situated just one block from Snow Hill's parks, playgrounds, public boat ramp, and the scenic Pocomoke River, this property offers the best of Eastern Shore living. Spend your days boating, kayaking, paddleboarding, fishing, crabbing, or enjoying a relaxing walk through historic downtown Snow Hill, all just steps from your front door. The thoughtfully designed interior features a bright open layout, an impressive kitchen with white cabinetry, stainless steel appliances, a spacious island, and a beautifully updated bathroom with a double vanity. Every room reflects the quality and care put into the home's extensive renovation. Located within the highly regarded Worcester County Public School District, this home is ideal for families, retirees, first-time buyers, or investors looking for a turnkey opportunity. With its unbeatable location, it also offers outstanding potential as a vacation home or Airbnb. Conveniently located: Approximately 25 minutes to Ocean City, Maryland Approximately 30 minutes to Assateague Island National Seashore Approximately 35 minutes to Chincoteague Island, Virginia Just a short drive to Salisbury for shopping, dining, healthcare, and Salisbury Regional Airport. Whether you're searching for your forever home, a weekend retreat, or an income-producing investment, this fully renovated property delivers exceptional value at $279,995. Don't miss your opportunity to own a like-new home in one of Maryland's most charming waterfront towns!

409 W Market St, Snow Hill

Listing courtesy of Keller Williams Realty. Contact: 3023600300

$2,490,000
5 Beds 6 Baths
Welcome to one of Ocean Pines’ most extraordinary waterfront estates, where luxury, recreation, and coastal living come together in a truly one-of-a-kind offering. Situated on a beautifully positioned waterfront homesite with 75 feet of newly bulkheaded shoreline, this remarkable residence encompasses approximately 9,200 square feet of thoughtfully designed living space with 5 bedrooms, 5.5+ baths, and an unmatched collection of resort-style amenities. Designed for entertaining on every level, the home features a spectacular 63-foot indoor pool with a 7-foot depth, private locker room, movie theater, expansive game room with wet bar, sunroom, and an oversized chef’s kitchen that opens seamlessly into light-filled living and dining spaces framed by soaring ceilings and walls of glass overlooking the water. The outdoor living experience is equally impressive. Enjoy expansive waterfront decking, an enclosed brick courtyard with a charcoal grill, multiple spaces for gathering, a rooftop observation deck with panoramic views, and direct boating access from your private dock featuring an 8,000-pound boat lift. Whether hosting family and friends or enjoying a quiet evening overlooking the water, every space has been designed to embrace the coastal lifestyle. Additional highlights include a two-car garage, generous driveway and guest parking, and the home is offered fully furnished (with select exclusions), allowing you to begin enjoying it from day one. Properties of this caliber are exceptionally rare. Whether you’re searching for an extraordinary primary residence, an unforgettable coastal retreat or the ultimate waterfront investment property, 23 Mallard Drive East delivers a lifestyle few properties can match. Schedule your private showing today and discover what life on the water was meant to be!

23 Mallard Dr E, Ocean Pines

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact: (410) 524-0919

$817,500
3 Beds 2 Baths
Live the ultimate West Ocean City waterfront lifestyle in the highly sought-after Cape Isle of Wight community. Situated on an oversized waterfront lot with approximately 80 feet of bulkheaded canal frontage, multiple deeded boat slips, and panoramic bay and canal views, this exceptional property offers quick navigable access to Assawoman Bay, making it a dream for boaters, anglers, and outdoor enthusiasts. Step from your backyard onto your boat for a day of fishing, cruising to waterfront restaurants, exploring the Ocean City Inlet, or relaxing at nearby sandbars, then unwind with breathtaking sunsets from the covered porch or second-level balcony. Inside, this inviting coastal retreat features 3 spacious bedrooms, 2 full bathrooms, an open-concept floor plan, beautiful wood flooring, an updated kitchen with upgraded countertops and modern finishes, and large windows showcasing incredible water views. Recent and notable improvements add to the home's appeal, including an HVAC/heating system approximately 5 years old, a hot water heater approximately 9 years old, and solar panels installed in November 2021. The deck is approximately 10 years old, and the boat dock has been enhanced with new decking, providing a refreshed space to enjoy the waterfront and easy access to your boats and watercraft. Designed for waterfront living, the property also offers an attached two-car garage and a detached garage/carriage house ideal for a workshop, studio, hobby space, or additional storage. There's plenty of room for boats, jet skis, kayaks, paddleboards, golf carts, beach gear, and fishing equipment, plus an outdoor shower, oversized yard, and generous outdoor entertaining space. Just minutes from Ocean City's beaches, Boardwalk, marinas, waterfront dining, shopping, championship golf courses, and Assateague Island, this home offers the perfect balance of peaceful waterfront living and convenient access to the best of Maryland's Eastern Shore. Whether you're looking for a primary residence, vacation home, or weekend getaway, this is a rare opportunity to own one of West Ocean City's premier waterfront properties.

12623 Sheffield Rd, Ocean City

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777

$349,900
3 Beds 2 Baths
PRICE REDUCTION! Adorable and affordable! Built by American Homes, this charming, well-maintained 3-bedroom, 2-bath rancher is ideally located near the Swim & Racquet Club pool and White Horse Park. The bright, open floor plan features cathedral ceilings, a combined Living, kitchen and dining area, and a separate laundry room off the kitchen. Relax on the inviting front porch or enjoy the spacious rear deck. Recent updates include fresh paint, roof replacement with warranty (2019) , newer HVAC, newer washer and dryer, and refrigerator, new microwave stove and dishwasher. Newly LVP flooring in the living room, dining room, and kitchen, new carpet in bedrooms. New bathroom flooring and raised toilets. Encapsulated crawlspace. Enjoy this low-maintenance home near the White Horse park, pool and recreation center.

304 Ocean Parkway, Ocean Pines

Listing courtesy of PW Realty Sales, LLC. Contact: 4432298888

$334,000
4 Beds 2 Baths
This house has been remodeled from Top to Bottom ! Enjoy the huge Living Room with Vaulted Ceilings and generous room for entertaining. The eat-in kitchen provides plenty of space for cooking and dining. This open-concept house has 4 bedrooms and 2 full baths. The Primary bedroom has a new ensuite and walk-in shower. The large, center bedroom has two full closets. The third bedroom provides a nice space with a ton of natural light. The 4th bedroom offers privacy in the rear of the house. There is a flex space that would work great as a home office, playroom or den. You can enjoy the comfort of knowing you have a New Roof, 2 New HVAC units and New Windows. Mystic Harbor is a wonderful community offering pools, clubhouse, and tennis courts. Just outside of Ocean City and Assateague Island. This can be a great Primary residence or an affordable beach Getaway !

37 Anchor Way Dr, Berlin

Listing courtesy of ERA Martin Associates. Contact: 4107491818

$442,000
3 Beds 2 Baths
Well-kept 3BR/2BA rancher on a corner lot in the desirable Innerlinks at Ocean Pines. This spacious single story home offers cathedral ceilings in the living room, hardwood floors throughout the foyer, living room, dining room, and hallway. Kitchen features a large eat-in area, quartz countertops, gas cooking, and a new refrigerator (2024). Sunroom off the dining room offers year-round use with large windows, and steps down to a deck overlooking the trees. Master suite includes a new walk-in tile shower; two additional bedrooms complete the layout. Two-car garage has ample storage space with access to attic storage room with shelving and electricity. Lots of storage space up there. Recent updates: newer roof (2021), newer washer (2023), newer refrigerator (2024), fresh paint throughout (walls, doors, frames, baseboards), new hardware and lighted fans in all bedrooms/sunroom/kitchen, new carpet in all bedrooms, new bathroom and dining room lighting, and a washer/dryer hookup added in the hall closet. Nestled along the Robert Trent Jones-designed golf course, the desirable Innerlinks neighborhood offers sidewalk-lined streets just steps from the Ocean Pines Yacht Club, Marina, and two community pools. Boating enthusiasts will love the easy walk to the boat ramp and gas dock at the Yacht Club, with direct access to the Isle of Wight Bay. Don't miss this opportunity to become a resident in the Innerlinks neighborhood.

1 Links Ln, Berlin

Listing courtesy of Iron Valley Real Estate Ocean City. Contact: (443) 205-4007

$409,000
4 Beds 2 Baths
Welcome to 15 Raft! This sweet, fully updated home is tucked away on a charming cul-de-sac in the highly desirable Ocean Pines. Boasting incredible updates inside and out, features include brand-new vinyl siding on the home and shed, an updated front porch, and a refreshed back deck. Inside, you'll find fresh paint, new carpet, and beautiful new ceramic tiling in the kitchen and bathroom. The sparkling kitchen features gorgeous granite countertops and brand-new stainless steel appliances. Complete with a new washer and dryer, this turn-key coastal retreat is ready for you! Don't miss this coastal gem—schedule your tour today! Ocean Pines offers an impressive selection of resort-style amenities with both free and paid membership options available. The amenities include swimming pools, parks, playgrounds, walking trails, a championship golf course, pickleball and tennis courts, marina, yacht club, a community garden, and a vibrant community center. This home is a beautiful choice for a vacation getaway, investment property, or a primaryresidence. Daily conveniences—including grocery stores, pharmacies, healthcare, banks, and local restaurants just a few minutes away. Enjoy easy access to Ocean City's famous Boardwalk and beaches, Assateague Island National Seashore's wild horses and natural beauty, historic downtown Berlin's boutiques and cafés, numerous nearby golf courses, like Rum Pointe Seaside Golf Links, the Links at Lighthouse Sound, and Glen Riddle Golf Club, boating, fishing, and outdoor recreation, as well as Delaware beach destinations like Bethany Beach, Lewes, Rehoboth Beach, and Fenwick Island all within a 20-50 minute drive.

15 Raft Rd, Ocean Pines

Listing courtesy of Iron Valley Real Estate Charm City. Contact: 4108160066

$995,000
4 Beds 3 Baths
Steps to the beach and your own private dock, 103 Channel Buoy Road sits canal-front in the heart of Caine Keys II, one of North Ocean City's most coveted waterfront addresses. A private pier and boat dock sit steps from the back door, with the beach directly across the street — two of the Shore's most sought-after features on a single property. Inside, vaulted ceilings, skylights, and walls of glass create a bright, open atmosphere throughout, anchored by a stone gas fireplace in the great room. The kitchen features granite countertops and a full stainless steel appliance suite, and the waterfront deck offers generous space for outdoor living and entertaining. Four bedrooms, three full baths, and 2,248 square feet across a thoughtfully designed layout — no HOA. Major updates completed within the past two years include a new roof, water heater, appliances, pier, carpet, and all-new living room windows. Turnkey, fully furnished, and ready.

103 Channel Buoy Rd, Ocean City

Listing courtesy of Fred Louis Zamer. Contact: 5712498770

$1,300,000
4 Beds 3 Baths
Waterfront Home in Terns Landing – Ocean Pines 2nd lot in from the end of the canal wiwth Bay Views Welcome to this beautiful 4-bedroom, 2.5-bath waterfront home located in the highly sought-after Terns Landing section of Ocean Pines. Designed with an open and airy layout, this home features floor-to-ceiling windows that fill the space with natural light from nearly every angle, creating a bright and inviting atmosphere throughout. The spacious kitchen is highlighted by granite countertops, perfect for both everyday living and entertaining. Just off the main living area, step out onto the extra-large deck overlooking the canal, where you’ll enjoy peaceful water views and stunning vistas of the Isle of Wight Bay. The second-floor loft offers additional living space, ideal for a home office or lounge area, while the generously sized game room provides flexibility and could easily serve as a 5th bedroom. A convenient 2-car garage adds to the home’s functionality. Major updates include a bulkhead less than 10 years old, a brand-new roof (2026), and a new driveway (2025), offering peace of mind for years to come. Enjoy all the benefits of this amenity-rich community, ideal for year-round living or as a second home getaway. With everything Ocean Pines has to offer, this is a rare opportunity you don’t want to miss! This home was built above mean High Tide and to Florida Hurrican Code. Schedule your showing today—this one won’t last long! Property is being Sold “As Is” Seller and has included a 1 year Home Warranty. The second floor AC is now brand new just install 9/10/26

24 Stacy Ct, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$349,900
2 Beds 2 Baths
Enjoy easy one-level living in this charming 2-bedroom, 2-bath rancher located in the sought-after community of Ocean Pines. The functional floor plan offers comfortable living spaces, abundant natural light, and low-maintenance living—perfect as a primary residence, vacation getaway, or investment property. Large deck with storage shed attached. Ocean Pines residents enjoy an exceptional lifestyle with outstanding amenities, including indoor and outdoor swimming pools, tennis courts, scenic walking and biking paths, a dog park, community center, playgrounds, parks, and year-round activities. Conveniently located just minutes from Ocean City beaches, shopping, dining, golf, and marinas, this home offers the perfect blend of comfort, recreation, and coastal living.

170 Windjammer Rd, Ocean Pines

Listing courtesy of Coldwell Banker/Bud Church Rea. Contact: (410) 524-7888

$590,000
4 Beds 3 Baths
Quality Craftsmanship meets exceptional care in this beautifully maintained home, built by Piney Island Builders. Neatly nestled on a large private lot backing to peaceful woods in the heart of Ocean Pines, this home offers the perfect blend of comfort, privacy, and timeless appeal. Designed for easy living, the home features a spacious first-floor primary suite, providing convenience and flexibility for everyday life. Recent updates include a newer roof, composite decking, and updated kitchen appliances, allowing you to move in with confidence. Step outside and enjoy the beautifully landscaped Backyard, where you'll find a charming treehouse and plenty of space to relax, entertain, or simply take in the serene wooded setting. Recently updated crawl space encapsulation and dehumidifier ensure peace of mind. A large garage offers ample room for vehicles, storage, and hobbies. Two more outbuildings, a large shed, and an adorable greenhouse complete the yard. This exceptional home showcases quality construction, thoughtful updates, and a peaceful setting -making it a wonderful opportunity to enjoy all that Ocean Pines has to offer

20 Frigate Run, Ocean Pines

Listing courtesy of Coldwell Banker Realty. Contact: 4438562211

$339,000
4 Beds 3 Baths
Welcome to 205 6th Street in Pocomoke City! This beautifully renovated home was completely updated from top to bottom in 2022 and is truly move-in ready. This property offers a fantastic opportunity as a primary residence, vacation getaway, or investment property. Recent improvements include a new driveway, sump pump, dehumidifier, fully fenced backyard, and a newly added patio—providing peace of mind and the perfect space for outdoor entertaining and relaxation. Conveniently located just 30 minutes from Berlin and within easy reach of Virginia's Eastern Shore, you'll enjoy small-town charm with quick access to beaches, shopping, dining, and outdoor recreation. Don't miss your chance to own this beautifully updated home—schedule your private showing today!

205 6th St, Pocomoke City

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400

$2,795,000
5 Beds 6 Baths
Welcome to 12355 Southampton Drive, the crown jewel of Lighthouse Sound, one of the Eastern Shore's most prestigious waterfront golf communities. This is a rare opportunity to own arguably the finest homesite in the neighborhood, where this extraordinary custom residence captures sweeping panoramic views of Assawoman Bay and the sparkling Ocean City skyline from nearly every rear-facing room. A dramatic two-story foyer with a graceful curved staircase sets the tone, drawing your eye straight through the soaring great room to the breathtaking water beyond. The two-story family room is anchored by a stunning natural stone fireplace with gas insert, creating an unforgettable gathering space framed by walls of glass. Designed for both everyday living and effortless entertaining, the chef's kitchen features gas cooking, granite countertops, a large center island, breakfast bar, sunny dining nook, walk-in pantry, and a fully equipped butler's pantry complete with wet bar and sink. Every space is thoughtfully connected to the expansive rear decks, ensuring the spectacular views are always part of the experience. The luxurious first-floor primary suite is a true private retreat, offering direct deck access, uninterrupted bay views, two professionally organized walk-in closets, and a spa-inspired bath with dual vanities, soaking tub, and oversized walk-in shower. A private study, spacious dining room, and main-level laundry complete the first floor. Upstairs, an impressive open landing overlooks the great room below and leads to four generously sized guest suites, each with private vanity and dressing areas and convenient en-suite bath access, providing exceptional comfort for family and guests alike. The outdoor living is every bit as remarkable as the interior. Nearly 1,700 square feet of wraparound Trex decking spans the rear of the home across two levels, creating an unparalleled setting for morning coffee, sunset cocktails, entertaining under the stars, or relaxing around the fire pit while watching boats drift across the bay and the Ocean City skyline come alive each evening. During the summer, enjoy a front-row seat to the free fireworks display every Sunday evening, launched from Northside Park just across the bay, a spectacular tradition that can be enjoyed from the comfort of your own deck. Additional highlights include Brazilian cherry hardwood flooring throughout, an oversized three-bay garage with abundant storage for vehicles and water toys, recessed lighting, ceiling fans, and quality craftsmanship throughout. Residents of Lighthouse Sound enjoy championship golf, an elegant clubhouse, dining, and one of the most spectacular waterfront settings on Maryland's Eastern Shore. Luxury. Views. Lifestyle. Rare opportunity. This isn't simply a home, it's a front-row seat to one of the most breathtaking waterfront panoramas on the East Coast. Once you experience the views from 12355 Southampton Drive, everywhere else feels ordinary.

12355 Southhampton Dr, Bishopville

Listing courtesy of Northrop Realty. Contact: (302) 539-0800

$239,900
3 Beds 2 Baths
Charming and well-maintained older 3-bedroom, 2-bath home in Pocomoke City offering classic character with thoughtful updates. This move-in ready home features hardwood flooring throughout, a welcoming layout, central air conditioning, and a kitchen with new appliances and upgraded countertops. Washer and dryer are included for added convenience. Other recent improvements include replacement windows and encapsulated crawl space. Enjoy a private backyard perfect for relaxing, entertaining, or gardening. Detached garage Conveniently located near schools, parks, shopping, downtown and the scenic Pocomoke River. A wonderful opportunity for first-time buyers, downsizers, or anyone looking for comfort, charm, and convenience.

201 6th St, Pocomoke City

Listing courtesy of Hall Realty. Contact: 4104302000

$550,000
3 Beds 3 Baths
Welcome to 10541 Shady Drive in Berlin, a private Eastern Shore retreat offering an incredible opportunity as a primary residence, vacation getaway, or potential short-term rental. Surrounded by mature trees, this spacious home features multiple living and entertaining areas, hardwood floors, abundant natural light, a generous kitchen, cozy wood-burning stoves, and a game room with a pool table—providing plenty of space for family and guests to relax and enjoy. Outside, the private swimming pool and expansive deck create the perfect vacation-style setting for summer days, outdoor dining, and entertaining. Conveniently located near Berlin and within easy reach of Ocean City, beaches, dining, shopping, and area attractions, this property has all the ingredients for an exciting Airbnb or vacation-rental opportunity. Whether you’re looking for your own Eastern Shore escape or an investment property with guest-friendly amenities, Shady Drive is ready for your vision.

10541 Shady Dr, Berlin

Listing courtesy of KW Metro Center. Contact: (703) 564-4000